Studies toward the Synthesis of Iriomoteolide-2a: Construction of the C(6)-C(28) Fragment
Studies toward the Synthesis of Iriomoteolide-2a: Construction of the C(6)-C(28) Fragment
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Iriomoteolide-2a 的合成研究：C(6)-C(28) 片段的构建
DOI：
10.1021/acs.orglett.8b00542
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发表时间：
2018
期刊：
影响因子：
5.2
通讯作者：
Ye Tao
中科院分区：
文献类型：
--
作者：
Wang Lushun;Wu Fusong;Jia Xuelei;Xu Zhengshuang;Guo Yian;Ye Tao
以高效的方式合成了海洋大环内酯Iriomoteolide-2a(1)的适当官能化的高级C(6-28)片段(3)。1的C(6)-C(18)片段是通过乙烯基醚中间体的自由基环化和钯促进的氢化锡化/碘化反应制备的。通过Paterson Aldol反应和Peterson烯化反应构建了C(19)-C(28)片段。C(6)-C(18)和C(19)-C(28)片段的结合是通过Suzuki-Miyaura偶联反应完成的。
The synthesis of an appropriately functionalized advanced C(6–28) fragment (3) of the marine macrolide iriomoteolide-2a (1) has been achieved in a highly efficient manner. The C(6)–C(18) fragment of1is prepared via a radical cyclization of a vinyl ether intermediate and palladium-promoted hydrostannylation/iodination. Paterson aldol reaction and Peterson olefination are used to construct the C(19)–C(28) fragment. The union of the C(6)–C(18) and C(19)–C(28) fragments is accomplished via a Suzuki–Miyaura coupling reaction.